CN100345831C - Prepn process of high purity 2, 6-dichloro quinoxaline - Google Patents

Prepn process of high purity 2, 6-dichloro quinoxaline Download PDF

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Publication number
CN100345831C
CN100345831C CNB2005100956247A CN200510095624A CN100345831C CN 100345831 C CN100345831 C CN 100345831C CN B2005100956247 A CNB2005100956247 A CN B2005100956247A CN 200510095624 A CN200510095624 A CN 200510095624A CN 100345831 C CN100345831 C CN 100345831C
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quinoxaline
dichloro
preparation
dichloro quinoxaline
technical
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CN1772742A (en
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吴永虎
赵邦斌
何普泉
苏朝辉
陈克付
孙澎
丁云好
陆广美
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吴永虎
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Abstract

The present invention relates to a method for preparing 2, 6-dichloro quinoxaline which has high purity, belonging to the technical field of preparation of fine chemical industry products. The present invention has the technical scheme to provide a method for preparing 2, 6-dichloro quinoxaline which has high purity so that the technical problem is solved, wherein 2, 6-dichloro quinoxaline does not need to be purified many times, and the 2, 6-dichloro quinoxaline can be generally applied to agrochemical and especially medicine. The present invention has the technical key point that 1 portion of 6-chloro-2-hydroxy-quinozaline and 2.5 to 3.5 portions of chlorinating agents by molar ratio as reactants, and a catalyst are added into an organic solvent system; after the reactants and the catalyst are stirred, the temperature is raised until a reflux situation is obtained, and the reaction is carried out; after the reaction is finished, most of the solvent is removed, solvent and water are added, and a pH value is regulated to be from 6 to 7 by liquid alkali; decolouring agents are added, and filtration operation is carried out in a distillation still; after the organic solvent is removed, 2, 6-dichloro quinoxaline is obtained. The content of the 2, 6-dichloro quinoxaline is more than 99%. The 2, 6-dichloro quinoxaline can be widely applied to agrochemical industry and medicine industry. The range of use is greatly widened. The preparation method is simple, the technical process is simple and controllable, no investment increase of equipment is needed, and the labor amount is not increased.

Description

High purity 2, the preparation method of 6-dichloro-quinoxaline
Technical field: the invention belongs to the fine chemical product technology of preparing, particularly a kind of high purity 2, the preparation method of 6-dichloro-quinoxaline.
Background technology: at present, industrial synthetic 2, the content of a discharging of 6-dichloro-quinoxaline is only up to about 94%, as intermediate, its content can not satisfy follow-up synthetic requirement fully, makes it especially be subjected to bigger restriction in pharmaceutically application at agricultural chemicals.If need further to improve content, then need repeatedly to purify, but thus, both reduced yield significantly, increased production cost, increased the productive labor amount again.
Summary of the invention: technical problem to be solved by this invention is: provide a kind of need not repeatedly purify promptly can be at agricultural chemicals especially in the high purity 2 of widespread usage pharmaceutically, the preparation method of 6-dichloro-quinoxaline, and this preparation method's simple controllable.Its technical scheme is: the preparation method of a kind of high purity 2,6-dichloro-quinoxaline, and its technical characterictic is:
(1), with reactant 6 chloro-2-hydroxyl-quinoxalines and chlorizating agent by 1: 2.5～3.5 mole when catalyzer join in the organic solvent system, be warming up to after the stirring and reacted under the backflow situation 5～10 hours;
(2), reaction sloughs most solvent after finishing, and then adds solvent and water, regulate between pH value to 6～7 with liquid caustic soda;
(3), add activated carbon decolorizing after, be filtered to still kettle, promptly get 2, the 6-dichloro-quinoxaline after sloughing organic solvent.
Above-mentioned chlorizating agent is sulfur oxychloride or phosphorus oxychloride.
Above-mentioned catalyzer is DMF or DMA.
Above-mentioned organic solvent is a toluene.
Its technique effect is:
1, adopt that preparation method of the present invention produced 2,6-dichloro-quinoxaline, its content can be widely used in agricultural chemicals and pharmaceutical sector greater than more than 99%, have widened its use range greatly.
2, preparation method of the present invention is extremely simple, reliable, the technological process simple controllable, and facility investment is few, and labour intensity is low.
Embodiment:
110ml toluene, 8.4 gram 6-chloro-2-hydroxy quinoxalines, 1.6 gram DMF, 15 gram sulfur oxychlorides are put in the 250ml reaction flask that stirring, condenser and thermometer are housed, feed intake and finish, stirring is warming up to reflux state, maintain the temperature between 96～108 ℃, insulation reaction 6 hours, after finishing, reaction deviates from organic solvent and part unreacted chlorizating agent (mother liquor of about 85ml, mother liquor can be applied mechanically) completely.Under little negative pressure, in system, add the toluene of 80ml and the water of 40ml then, destroy remaining a small amount of SOCl 2(sulfur oxychloride), dropwise liquid is regulated pH value between the 6-7, add the 1g activated carbon decolorizing after Plate Filtration to still kettle, divide behind a small amount of floss of sub-cloud the water azeotropic to deviate from cooling sheet frame discharging behind about toluene of about 95%, washing, blow pressure gas promptly get 2 of 8.5g, the 6-dichloro-quinoxaline after the drying, GC analyzes content greater than 99.5%, and yield is greater than 96%.

Claims (4)

1, the preparation method of a kind of high purity 2,6-dichloro-quinoxaline, its technical characterictic is:
(1), with reactant 6 chloro-2-hydroxyl-quinoxalines and chlorizating agent by 1: 2.5～3.5 mole when catalyzer join in the organic solvent system, be warming up to after the stirring and reacted under the backflow situation 5～10 hours;
(2), reaction sloughs most solvent after finishing, and then adds solvent and water, regulate between pH value to 6～7 with liquid caustic soda;
(3), add activated carbon decolorizing after, be filtered to still kettle, promptly get 2, the 6-dichloro-quinoxaline after sloughing organic solvent.
2, a kind of preparation method according to claim 1 is characterized in that: described chlorizating agent is sulfur oxychloride or phosphorus oxychloride.
3, a kind of preparation method according to claim 1 is characterized in that: described catalyzer is DMF or DMA.
4, a kind of preparation method according to claim 1 is characterized in that: described organic solvent is a toluene.
CNB2005100956247A 2005-11-10 2005-11-10 Prepn process of high purity 2, 6-dichloro quinoxaline Active CN100345831C (en)

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CNB2005100956247A CN100345831C (en) 2005-11-10 2005-11-10 Prepn process of high purity 2, 6-dichloro quinoxaline

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Application Number Priority Date Filing Date Title
CNB2005100956247A CN100345831C (en) 2005-11-10 2005-11-10 Prepn process of high purity 2, 6-dichloro quinoxaline

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CN100345831C true CN100345831C (en) 2007-10-31

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Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101914069A (en) * 2010-07-29 2010-12-15 安徽丰乐农化有限责任公司 Novel chlorination technique of 6- chlorine-2-hydroxy quinoxaline

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4083977A (en) * 1974-09-19 1978-04-11 Eli Lilly And Company Novel insecticidal 1-(substituted benzoyl)-3-(substituted pyrazinyl)ureas
US4160384A (en) * 1977-06-01 1979-07-10 Carl Schenck Ag Process for the turning-in of a part to be balanced affected by imbalance
US4582526A (en) * 1982-12-17 1986-04-15 Hoffmann-La Roche Inc. Carbamic acid ester herbicides
US4636562A (en) * 1982-05-07 1987-01-13 E. I. Du Pont De Nemours And Company Process for preparing 6-halo-2-chloroquinoxaline
WO1991001977A1 (en) * 1989-08-05 1991-02-21 Hoechst Aktiengesellschaft Process for preparing 2,6-dicholoroquinoxaline
EP0672662A1 (en) * 1994-03-04 1995-09-20 Eli Lilly And Company Quinoxaline derivative used in the treatment of tumours

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4083977A (en) * 1974-09-19 1978-04-11 Eli Lilly And Company Novel insecticidal 1-(substituted benzoyl)-3-(substituted pyrazinyl)ureas
US4160384A (en) * 1977-06-01 1979-07-10 Carl Schenck Ag Process for the turning-in of a part to be balanced affected by imbalance
US4636562A (en) * 1982-05-07 1987-01-13 E. I. Du Pont De Nemours And Company Process for preparing 6-halo-2-chloroquinoxaline
US4582526A (en) * 1982-12-17 1986-04-15 Hoffmann-La Roche Inc. Carbamic acid ester herbicides
WO1991001977A1 (en) * 1989-08-05 1991-02-21 Hoechst Aktiengesellschaft Process for preparing 2,6-dicholoroquinoxaline
EP0672662A1 (en) * 1994-03-04 1995-09-20 Eli Lilly And Company Quinoxaline derivative used in the treatment of tumours

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
A FACILE SYNTHESIS OF NOVEL TRICYCLICCOMPOUND,TETRAZOLOQUINOXALINES AND1,2,4-TRIAZOLOQUINOXALINES Kenzi Makino,et al,HETEROCYCLES,Vol.23 No.(8) 0198 *
THE SYNTHESISI OF NOVEL2-(2-QUINOXALINYL)PYRIDAZIN-3(2H)-ONES Kenzi Makino,et al,HETEROCYCLES,Vol.23 No.(10) 1985 *
喹禾灵的合成 高学民等，农药，第37卷第(7)期 1998 *

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